This one is short and sweet - great views of Rainier, and the lookout is perched precariously on top of the rock which is truly fun. Maybe you can snowshoe if access road is snow free most of the way.
Lookout Structure Details for High Rock Lookout: Open to the Public
White Pass Historical Museum/USFS
It was open to the public last time we were there and in decent shape. However, all info says day use only. Do not plan to overnight in it. Last I read the lookout was removed for repair but is scheduled to be returned summer of 2025. The trail is closed until its return.